So I'm starting to dabble in type design and have been messing around with the calligraphic brushes in illustrator.

I've skeletoned out some letter forms with lines and curves. I would now like to apply a calligraphic stroke, but I would like the nib/tip of the calligraphic brush to be a rounded rectangle and not oval shaped. There doesn't seem to be an advanced options area for calligraphic brushes. I almost reached the affect by making the rounded rectangle shape into a scatter brush and reducing the spacing, but the minimum spacing is 10% (I would need 0%).

Is there any way to create this affect? Is there any way to create a calligraphic brush with a custom shaped nip/tip?

Jason, typographic letterforms are not "expanded skeletons".
It might be tempting to think of the process you're following
as adequate for a beginner; I'd counter that it's a damaging
foundation for future development.

Try to think of a font as a collection of black and
white shapes that "talk to each other" to form words.

Now that I think about it there was an Illustrator plugin for doing this called LivePen. But it was Windows only, so it was pretty much irrelevant to designers and FontLab bought it and withdrew it from the market. Maybe you can get them to sell you a copy.

> I understand that type design in very detailed and intricate process.
> I am trained in the fine arts and know the proper way to approach a project like such.

Type design is not a fine art, it's a craft, like architecture or furniture design.

What fine arts training do you have that includes type design training? Unless you have *specifically" studied type design (whether formally or not), you don't know how to approach it. This doesn't mean you shouldn't, or shouldn't learn. Note also that type design is not the same thing as calligraphy.

> My current endeavor takes my down an alternate path. This font is based deeply in mathematics and precision,
> hence it's creation in a computer program.

Modern typefaces are pretty much *all* created in computer programs. It's just that most type designers use dedicated type design programs to do it. Maybe half of them do sketches first, and about as many do not.